CN106588624B - A kind of preparation method of lactic acid - Google Patents
A kind of preparation method of lactic acid Download PDFInfo
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- CN106588624B CN106588624B CN201611122096.4A CN201611122096A CN106588624B CN 106588624 B CN106588624 B CN 106588624B CN 201611122096 A CN201611122096 A CN 201611122096A CN 106588624 B CN106588624 B CN 106588624B
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- lactic acid
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Abstract
The present invention provides a kind of preparation methods of lactic acid.The present invention is using saccharide compound as raw material, through Ba (OH) under ball milling condition2·8H2O catalysis carries out glycolysis and reacts to obtain lactic acid.The experimental results showed that preparation method the substrate transformation rate provided by the invention is up to 99.2%, lactic acid yield is up to 36.5%.Preparation method provided by the invention is easy to operate, mild condition, low energy consumption, low in cost, technique is easily-controllable, is suitable for that large-scale industry is promoted.
Description
Technical field
The present invention relates to biomass trans-utilization technical field, in particular to a kind of preparation method of lactic acid.
Background technique
In recent years, environmental pollution and energy consumption to carry out being prepared for fuels and chemicals with renewable resource
More concerns.Biomass is the photosynthetic product of plant cell, including in addition to fossil fuel it is all from animals and plants,
It can regenerated organic substance.Biomass energy has resourceful, the wide, purposes of distribution as unique reproducible carbon resource
It can be converted the characteristics of a variety of secondary energy sources etc. are different from other renewable energy extensively, thus increasingly by the blueness of people
It looks at.Carbohydrate can be converted into a variety of important platform chemicals, including formic acid, second as one of important biomass resource
Acid, levulic acid, lactic acid, 5 hydroxymethyl furfural etc., such correlative study and document have more report.
Lactic acid is universally acknowledged one of three big organic acids, is a kind of important chemical platform compound.It is widely present
In in human body and other organic-biological bodies, play an important role in anaerobic metabolic process.Lactic acid and its polymer and lactate etc.
There is very important status in fields such as food, medicine, chemical industry, the demand of lactic acid is estimated other up to several hundred 10,000 tons, so
And its yield and demand still have huge notch.
Currently, 90% business lactic acid is made by fermentation method, but the production cycle of zymotechnique is longer, efficiency compared with
It is low, it is influenced in fermentation process vulnerable to temperature, pH etc., it is at high cost, and a large amount of solid waste can be generated in production process.Therefore,
Chemical method prepares the hot spot that lactic acid is increasingly becoming current research.Lactic acid is directly prepared by the way that catalyst is added using carbohydrate as raw material
The production cost that lactic acid can be significantly reduced meets the requirement of Green Chemistry.
The scheme that catalysis carbohydrate reported in the literature prepares lactic acid includes that acid and base catalysis, acidic catalyst refer to utilization
Homogeneous or out-phase bronsted acid or lewis acid are catalyst, including zeolite, carbon support materials, metal material and more metals
Oxide etc..Base catalysis refers to that using the hydroxide of alkali metal and some organic bases be catalyst.Base catalysis uses model
It encloses larger, is the method that a kind of currently used sugared catalysis prepares lactic acid.However most of catalytic process is required in higher temperatures
Degree is lower to carry out, and maintains certain pressure, and common temperature range is 120~300 DEG C, and pressure is 0.5~3MPa, is unfavorable for
Industrial operation, and many catalyst need additional step to be prepared, and increase workload and cost.
Summary of the invention
The purpose of the present invention is to provide the preparation methods for the lactic acid that the easy to operate and raw material of one kind is easy to get.
The present invention provides a kind of preparation methods of lactic acid, by saccharide compound and Ba (OH)2·8H2O carries out ball milling, obtains
To lactic acid.
Preferably, the saccharide compound and Ba (OH)2·8H2The mass ratio of O is 3~9:1.
Preferably, the saccharide compound and Ba (OH)2·8H2The mass ratio of O is 4~8:1.
Preferably, the ratio of grinding media to material of the ball milling is 5~20:1.
Preferably, the revolving speed of the ball milling is 400~600r/min.
Preferably, the time of the ball milling is 2~6h.
Preferably, the saccharide compound includes one of monosaccharide and disaccharides or a variety of.
Preferably, the monosaccharide include one of glucose, fructose, mannose, galactolipin, arabinose and ribose or
It is a variety of.
Preferably, the disaccharides includes one of cellobiose, lactose and maltose or a variety of.
The present invention provides a kind of preparation methods of lactic acid.The present invention is using saccharide compound as raw material, under ball milling condition
Through Ba (OH)2·8H2O catalysis carries out glycolysis and reacts to obtain lactic acid.The experimental results showed that preparation method substrate provided by the invention
Conversion ratio is up to 99.2%, and lactic acid yield is up to 36.5%.Preparation method provided by the invention is easy to operate, mild condition, energy
It consumes that low, low in cost, technique is easily-controllable, is suitable for that large-scale industry is promoted.
Detailed description of the invention
Fig. 1 is that the products collection efficiency that Examples 1 to 3 obtains and the substrate transformation rate change over time curve；
Fig. 2 is that the obtained products collection efficiency of embodiment 2 and 4 and the substrate transformation rate with catalyst and substrate quality compare change profile
Figure；
Fig. 3 is the products collection efficiency that embodiment 2,5 and 6 obtains and the substrate transformation rate with substrate gross mass change profile figure；
Fig. 4 is the products collection efficiency that embodiment 2,7 and 8 obtains and the substrate transformation rate with abrading-ball quantity change profile figure；
Fig. 5 is the products collection efficiency that embodiment 2 and 9~17 obtains and the substrate transformation rate with substrate kind change profile figure.
Specific embodiment
The present invention provides a kind of preparation methods of lactic acid, by saccharide compound and Ba (OH)2·8H2O carries out ball milling, obtains
To lactic acid.In the present invention, under the ball milling condition, the saccharide compound is at Ba (OH)2·8H2Ferment occurs under O catalytic action
Solution reaction, obtains lactic acid, the saccharide compound and Ba (OH)2·8H2The mass ratio of O is preferably 3~9:1, more preferably 4~
8:1, most preferably 5~6:1.
In the present invention, the saccharide compound preferably includes one of monosaccharide and disaccharides or a variety of.In the present invention,
The monosaccharide preferably includes one of glucose, fructose, mannose, galactolipin, arabinose and ribose or a variety of.In this hair
In bright, the disaccharides preferably includes one of cellobiose, lactose and maltose or a variety of.
The present invention does not have special restriction to the type of the abrading-ball of the ball milling, using mill well known to those skilled in the art
Ball.In the present invention, the material of the abrading-ball is preferably zirconium oxide；The diameter of the abrading-ball is preferably 0.8~1.2cm；
The quality of the abrading-ball is preferably 1.5~2.5g.
In the present invention, the ratio of grinding media to material of the ball milling is preferably 5~20:1, more preferably 10~15:1.In the present invention,
The revolving speed of the ball milling is preferably 400~600r/min, more preferably 450~550r/min.In the present invention, the ball milling
Time is preferably 2~6h, more preferably 3~5h.In the present invention, in the mechanical milling process, saccharide compound is at Ba (OH)2·
8H2Reaction obtains lactic acid and by-product under the catalytic action of O.In the present invention, the by-product preferably include formic acid, acetic acid,
One of glycolic, glyceric acid, glyceraldehyde and fructose are a variety of.
After the completion of ball milling, the present invention preferably mixes the ball milling product with acid solution, obtains acidizing product, then will be described
Acidizing product is separated, and lactic acid and various by-products are respectively obtained.In the present invention, the acid solution is preferably inorganic acid
Aqueous solution；The inorganic acid is preferably sulfuric acid.In the present invention, the molar concentration of the acid solution be preferably 0.4~
0.6mol/L.In the present invention, the sulfuric acid and Ba (OH)2·8H2The molar ratio of O is preferably not lower than 1:1.
The not special restriction of operation of the present invention to the separation, is separated using lactic acid well known to those skilled in the art
The technical solution of purification.In the present invention, the separation is preferably liquid chromatogram separation.In the present invention, the liquid phase
Chromatographic column is preferably shodex SH1011 chromatographic column；The temperature of the liquid-phase chromatographic column is preferably 45~55 DEG C；The liquid phase color
Composing the mobile phase in column is 4~5mM H2SO4；The flow velocity of the mobile phase is 0.4~0.5mL/min
In order to further illustrate the present invention, it is carried out below with reference to preparation method of the embodiment to lactic acid provided by the invention detailed
It carefully describes, but they cannot be interpreted as limiting the scope of the present invention.
Embodiment 1:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g glucose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
2h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 92.8% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 26.7%.
Embodiment 2:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g glucose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.3% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 34.2%.
Embodiment 3:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g glucose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
6h obtains lactic acid.
20mL0.5M H is used after the reaction was completed2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.From
Supernatant measures the substrate transformation rate and lactic acid yield into liquid chromatogram after the heart.
It is 97.8% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 36.5%.
Embodiment 4:
Take 1.8g Ba (OH)2·8H2O, then weigh 0.2g glucose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 98.2% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 35.4%.
Embodiment 5:
Take 0.75g Ba (OH)2·8H2O, then weigh 0.25g glucose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 99.2% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 34.1%.
Embodiment 6:
Take 3g Ba (OH)2·8H2O, then weigh 1g glucose and be mixed with.The ball grinder of 40mL tetrafluoroethene is added, takes
10 1 centimetre of diameter, the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, and Ball-milling Time 4h is obtained
Lactic acid.
20mL0.5M H is used after the reaction was completed2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.From
Supernatant measures the substrate transformation rate and lactic acid yield into liquid chromatogram after the heart.
It is 94.6% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 35.1%.
Embodiment 7:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g glucose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 5 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time 4h,
Obtain lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 96.6% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 34.4%.
Embodiment 8:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g glucose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 20 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.2% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 34.9%.
Embodiment 9:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g fructose and be mixed with.The ball grinder of 40mL tetrafluoroethene is added,
1 centimetre of 10 diameters are taken, the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, and Ball-milling Time 4h is obtained
To lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.3% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 35.5%.
Embodiment 10:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g mannose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.1% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 34.9%.
Embodiment 11:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g galactolipin and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 96.8% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 31.9%.
Embodiment 12:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g xylose and be mixed with.The ball grinder of 40mL tetrafluoroethene is added,
1 centimetre of 10 diameters are taken, the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time 4h.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.5% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 33.9%.
Embodiment 13:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g arabinose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 96.8% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 32.7%.
Embodiment 14:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g ribose and be mixed with.The ball grinder of 40mL tetrafluoroethene is added,
1 centimetre of 10 diameters are taken, the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, and Ball-milling Time 4h is obtained
To lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.8% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 36.3%.
Embodiment 15:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g cellobiose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h。
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.2% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 29.8%.
Embodiment 16:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g lactose and be mixed with.The ball grinder of 40mL tetrafluoroethene is added,
1 centimetre of 10 diameters are taken, the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, and Ball-milling Time 4h is obtained
To lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 96.5% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 32.1%.
Embodiment 17:
Take 1.5g Ba (OH)2·8H2O, then weigh 0.5g maltose and be mixed with.The ball milling of 40mL tetrafluoroethene is added
Tank takes 1 centimetre of 10 diameters, and the zirconia ball that quality is about 2g carries out ball milling.Ball milling speed is 500r/min, Ball-milling Time
4h obtains lactic acid.
With 20mL0.5M H2SO4Neutralization and acidizing product, while removing Ba2+Influence to chromatographic column.Centrifuged supernatant
The substrate transformation rate and lactic acid yield are measured into liquid chromatogram.
It is 97.2% that the present embodiment, which obtains the substrate transformation rate, lactic acid yield 31.5%.
The products collection efficiency and the substrate transformation rate that Examples 1 to 3 obtains change over time curve graph as shown in Figure 1, can from Fig. 1
To find out, the yield of the conversion ratio of substrate, lactic acid and various by-products is improved with the increase of Ball-milling Time, when Ball-milling Time reaches
Start to tend to be steady when to 2h, when Ball-milling Time is 2~6h, the conversion ratio of substrate is higher, the yield of lactic acid and various by-products
It is high.
Products collection efficiency that embodiment 2 and 4 obtains and the substrate transformation rate with catalyst and substrate quality such as than change profile figure
Shown in Fig. 2, when the gross mass of catalyst and substrate is constant, figure it is seen that the mass ratio of catalyst and substrate be 3~
When 9:1, the high conversion rate of substrate, and the yield of lactic acid is high.
The products collection efficiency and the substrate transformation rate that embodiment 2,5 and 6 obtains are with substrate gross mass change profile figure such as Fig. 3 institute
Show, when the mass ratio of catalyst and substrate is constant, from figure 3, it can be seen that the conversion ratio of substrate, the production of lactic acid and each by-product
Rate is basically unchanged.
The products collection efficiency and the substrate transformation rate that embodiment 2,7 and 8 obtains with abrading-ball quantity change profile figure as shown in figure 4,
When the quality of catalyst and substrate is constant, from fig. 4, it can be seen that the conversion ratio of substrate, the yield of lactic acid and each by-product
The yield of the conversion ratio of substrate when abrading-ball number is 5~20 (i.e. 5~20:1 of ratio of grinding media to material), lactic acid and each by-product is higher.
The products collection efficiency and the substrate transformation rate that embodiment 2 and 9~17 obtains are with substrate kind change profile figure such as Fig. 5 institute
Show, from fig. 5, it can be seen that the conversion ratio of different saccharide compounds is higher using preparation method provided by the invention, lactic acid is produced
Rate is higher.
As can be seen from the above embodiments, the lactic acid of preparation method preparation provided by the invention has high-specific surface area, system
Standby carbon electrode is used to have good chemical property when super capacitor.
The above is only a preferred embodiment of the present invention, it is not intended to limit the present invention in any form.It should
It points out, for those skilled in the art, without departing from the principle of the present invention, if can also make
Dry improvements and modifications, these modifications and embellishments should also be considered as the scope of protection of the present invention.
Claims (8)
1. a kind of preparation method of lactic acid, by saccharide compound and Ba (OH)2·8H2O carries out ball milling, obtains lactic acid；The carbohydrate
Compound is one of monosaccharide and disaccharides or a variety of.
2. preparation method according to claim 1, which is characterized in that the saccharide compound and Ba (OH)2·8H2The matter of O
Amount is than being 3~9:1.
3. preparation method according to claim 2, which is characterized in that the saccharide compound and Ba (OH)2·8H2The matter of O
Amount is than being 4~8:1.
4. preparation method according to claim 1, which is characterized in that the ratio of grinding media to material of the ball milling is 5~20:1.
5. preparation method according to claim 1 or 4, which is characterized in that the revolving speed of the ball milling is 400~600r/
min。
6. preparation method according to claim 5, which is characterized in that the time of the ball milling is 2~6h.
7. preparation method according to claim 1, which is characterized in that the monosaccharide include glucose, fructose, mannose,
One of galactolipin, arabinose and ribose are a variety of.
8. preparation method according to claim 1, which is characterized in that the disaccharides includes cellobiose, lactose and malt
One of sugar is a variety of.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103626633A (en) * | 2013-11-14 | 2014-03-12 | 中国科学院广州能源研究所 | Method for promoting solid catalyst to depolymerize cellulose |
| CN105777523A (en) * | 2016-04-07 | 2016-07-20 | 农业部环境保护科研监测所 | Method for preparing lactic acid from carbohydrates in mild conditions |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103626633A (en) * | 2013-11-14 | 2014-03-12 | 中国科学院广州能源研究所 | Method for promoting solid catalyst to depolymerize cellulose |
| CN105777523A (en) * | 2016-04-07 | 2016-07-20 | 农业部环境保护科研监测所 | Method for preparing lactic acid from carbohydrates in mild conditions |
Non-Patent Citations (2)
| Title |
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| Production of D-lactic acid from hardwood pulp by mechanical milling followed by simultaneous saccharification and fermentation using metabolically engineered Lactobacillus plantarum;Shinji Hama;《Bioresource Technology》;20150328;167-172 |
| 中低热固相反应研究进展;蔡艳华;《化工技术与开发》;20090630;第38卷(第6期);22-28 |
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